International Journal of Organic Chemistry

Volume 7, Issue 1 (March 2017)

ISSN Print: 2161-4687   ISSN Online: 2161-4695

Google-based Impact Factor: 1.15  Citations  

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

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DOI: 10.4236/ijoc.2017.71006    2,134 Downloads   4,052 Views  Citations

ABSTRACT

A novel 2-indano[2,3b]-2-ferrocenyl- and 2-indano[2,3b]-2-(p-methoxy-phenyl)[1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl- and 2-(p-methoxyphenyl)[1,4] benzothiazine 4a,b (addition “anti-Michael”/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxy-phenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new “anti-Michael” addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported. As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, 1H and 13C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.

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García, J. , Hernández-Suzan, A. , Martínez-Klimova, E. , Flores-Alamo, M. , Apan, T. and Klimova, E. (2017) “Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol. International Journal of Organic Chemistry, 7, 57-81. doi: 10.4236/ijoc.2017.71006.

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